Jennifer Mackey-Mary: Hello Gorgeous! 

Welcome back to the last episode of The Everyday Style School: Summer Shorts–our weekly summer series sharing a quick style thought or  tip to help you save money, save time, and get the wardrobe you’ve always wanted.

I’m your host, Jennifer Mackey-Mary. I’ve been dressing women for 25 years, and I’m on a mission to help you love the way you look every day. 

In today’s tip, we’re talking about one of the biggest reasons the style advice you’ve gotten in the past hasn’t actually helped you become more stylish. I know you’ve probably read a magazine article or a blog post, maybe even mine, about what you should wear for your body type. I know lots of you have had your colors done, and carry your little color cards in your bag. But I also know that even armed with the knowledge that should make all of this easier, many women still struggle. If that describes you, you’re not alone. You’re not bad at style, and your body isn’t too weird to fit in a category. you’ve simply had the wrong approach to style. You wanna know how to fix it? Here it is–Stop memorizing rules, start learning strategies. 

In this episode, I want to talk about the difference between rules and strategies, why we love rules and resist strategies, what’s wrong with a rule-based approach to style and what to do instead. 

That’s a lot for a mini episode, so let’s get to it, starting with what the difference is. When I say rule, you probably think something like “Apples shouldn’t wear drop shoulder tops” or “you can’t wear white after labor day”, which, in the year of our lord two thousand and twenty five, is not a thing anymore, please let it go..and yes, those are rules. But for this discussion, I want you to think a little broader with this definition. Rules are the answer, strategies are the why behind it, or how did we get there. Let’s use white after labor day as an example. That’s the rule. Don’t wear white after labor day. But why? How did we get there? Most people have no idea. 

Lucky for you, I’m not most people, and I know, and I’m going to share it with you. Over a century ago, wealthy people used to wear white clothing–especially light fabrics like linen or cotton lawn, when they were away from the city during the summer. These light colored, hard to keep clean fabrics signaled a time of leisure, and when they returned to the city at the end of summer ie, labor day, their whites got put away. So unless you’re a Vanderbilt living in the Gilded age, this rule doesn’t really apply to you. 

We’ve been hanging on to a rule, without any idea of the strategy behind it. The strategy here is about wearing clothes that are appropriate in context. So are white linen pants appropriate in Minnesota in February? Probably not. Are white linen pants appropriate in South Floriday in February? Probably. Its all about context.

When you hear wear this, don’t wear that, do this, don’t do that without understanding why, that’s a rule. When you dig into the why, or understand how we got to that answer, that’s the strategy. 

In my decades of dressing women, its been my experience that women crave rules and resist strategies, and I think there are few reasons for this but the biggest one is that rules are easy. Just tell me what to wear. Just tell me what to buy. Give me a checklist. On the surface, rules seem like the fastest, easiest way to get a flattering, stylish wardrobe. Strategies, on the other hand, require effort. A few weeks ago, I posted on Instagram, stop asking, Can I wear this, and instead ask, what will this do for me. For example, can a petite woman wear a midi skirt. It’s a quick yes or no answer right? That’s a rule. The strategy asks, what will that midi skirt do for me? That’s a bigger question that requires an understanding of your body shape and your goals, as well as what the individual elements of that skirt–like lines and volume, do for every body. Then you have to match those things up to your body. Is a line across your calf a good thing, or not? Does your body look best with volume on the bottom or not? At first glance, just tell me yes or no is a whole lot easier.

But if you’ve tried to follow style rules to dress better, and you’re still struggling, you’ve experienced the limitations of rules. Now, you probably just thought it was you, and your body is weird, or you’re just doing it wrong, but I’m willing to bet that’s not the case at all. Here are just a few problems with rules–and why strategies actually make style easier in the long run.

First, rules don’t allow for nuance.
Let’s go back to can petites wear midi skirts? Some sites say yes, some say no. Either way, its a rule. Now, if you were to ask me that question, i would ask you, what kind of midi? A full, drop waist midi, or a narrow column? What’s your horizontal body shape? What’s your vertical body shape? What kind of top are you going to wear with that specific skirt? What kind of shoes are you going to wear? 

The rule is either going to make you think that all midis are terrible for you and you won’t try at all, or all midis are going to be great, and you might end up wondering why you don’t like the way you look–after all, the skirt was supposed to work. The strategy is going to help you understand why some midis will work better than others, and what to do if you’re not loving the way you look in the skirt. It’s more work, but in the end, the strategy will help you find a skirt you love. Rules are general, but people and clothes are nuanced, and need a nuanced approach

My second issue with rules is that they can’t cover everything.
Let’s take colors for example. I’m a big fan of Jeannie from Color Guru–we’ve had her on the show, and I love her modern take on colors. As I record this, my color card is sitting right on my desk, showing me the 35 best colors for me–that’s the rule. 35 sounds like a lot, and it is, but do you mean to tell me these are the ONLY colors that look good on me? What about a shade green that falls right between the two greens on my card? Should I avoid that one? If I’m following the rule, yes. However, I know the strategy behind my best colors, which is that I look best in colors that are light, bright, and warm. So instead of having to hold up my card to my computer monitor, or the tshirt in the store, and find a perfect match, I can ask, is it light bright and warm? If yes, it will probably be a winner, and I’m no longer reliant on a 4x6 card to find things I look good in.

When it comes to body shapes, there are hundreds of sites sharing rules about what body types should and shouldn’t wear. I went to one I think is very well done and pretty comprehensive, and looked at jackets. It lists 4 jacket styles for each shape. For any body there are more than 4 jackets that will look nice on you. But if you’re someone who loves a rule and is committed to looking your best, you’ll probably feel like those are your only choices.

Another issue is that rules are often contradictory. And this happens in two ways. First, it’s two different sources giving conflicting rules. For example the midi skirt. One site says petites should avoid them because they make you look shorter, one site says petites should wear them because they make you look taller. I’ve seen this happen with raglan sleeves, dolman sleeves, peplums–a million things. The rule depends on the source. This is when you need an understanding of strategy, or the why behind the rule, to weed out what’s true for you and what isn’t

But contradictions don’t always come from missguided advice. Sometimes both things can be true, and still contradict. Let’s use color and body shape. For my body, which is bigger on top than on bottom, the rule says I need to wear dark colors on top. However, my coloring says put light colors near my face. What’s a girl to do? Lots of women take rules as unbreakable gospel, and when they contradict, they’re stuck. However, strategy tells me that color is ONE way to balance my top and bottom, and if that doesn’t work, I can still rely on lines, pattern, and volume, to achieve balance. You know that phrase–there’s more than one way to skin a cat? That’s strategy. I don’t know who’s skinning cats, but if you are, please stop. 

My last issue with rules is that they don’t keep up with change very well. A lot of the sites handing out wear this not that body type rules are still talking about who can wear skinny jeans. That’s cool, but who can wear barrel legs. That’s what women want to know right now. When you’re a rule follower, and a new style is trending, if there’s not a published rule for it, you’re stuck, and probably don’t even try. You need a new rule for every new thing. Strategies, on the other hand, never change. You just apply them to a new situation. Horizontal lines will always make the body part they fall on look wider. Always. So it doesn’t matter if crop tops or tunics are trending, you know what they’ll do for your body. This applies to when YOU change as well. Lots of women get stuck when their bodies change and the rules they’ve always relied on no longer serve them. Knit fabrics will always cling, woven fabrics will always glide. If you used to be someone who liked to highlight your waist, and now you don’t, you don’t need to start from scratch with a whole new set of rules to tell you what you can and can’t wear, you just need to utilize a different strategy. 
This was highlighted for me when we did the Is it Dated podcasts a few months ago. In them I shared some pieces I see women wearing that aren’t current anymore, as well as strategies for determining if the piece in question was still current or not, and how to train yourself to see what current styling looks like. Ironically, those podcast episodes will date. The pieces I talked about may look current again in 10 years, and other pieces will look dated. But the strategies I shared will work now, and they’ll still work in 10 years. When you rely on rules, you’ll need someone to give you new rules for life. You’re always starting over. When you learn strategies, you just apply them to a new situation, and change isn’t such a big deal. 

So does this mean that rules have no value at all? No, the issue is how we use them. Rules are a good starting point. My color card narrowed the infinite number of options out there, and put me on the right path. So helpful. But rules can only take you so far. When the green isn’t on the card, you need to understand why some colors work for you, and some dont. When the jackets you’re supposed to wear aren’t in stores, you need to know how to adapt. When you use rules as the final answer, not the starting point, you’re going to struggle.  If you want to make style easy for life, learning strategies is the only way to go. 

You know, I had planned on wrapping up this episode with what you should do instead, but I kind of feel like that’s beating a dead horse at this point. You should learn strategies. And if you’re wondering, but Jen, how do I learn the strategies–girl, that’s literally what we do!

Every class in our membership teaches you strategies instead of giving you rules. Signature Style doesn’t tell you how to bring my style vision to life, it teaches you how to define your ideal style, and how to bring that to life. Dress your body shape doesn’t tell you the 10 things you should wear or avoid, it teaches you to apply clothing elements like lines, proportion, color, volume, and fabric to your unique body to find clothes that make you feel fantastic. The Ultimate Closet Makeover doesn’t tell you what to get rid of, it teaches you the questions to ask yourself so you make good choices. None of the things you learn in those classes will be irrelevant next year or even in 10 years. If your body changes, you don’t need another class. If your style changes, or your lifestyle changes, you’ll know how to adapt. I don’t want you to look great for a season. I want you to be stylish for life.

I never want this show to be just a commercial for the Style Circle. I want you to get a ton of value from it whether you join or not. But I feel like I’d be doing a disservice by not sharing how what we do at Everyday Style is fundamentally different than a lot of style services out there. And I’m not going to lie to you, my way requires more effort in the beginning, but the payoff is life long–and that’s how style actually becomes easy. The quick answers will never get you there. If you’re ready to put down the rules, and start learning strategies, the link to join us is in the shownotes, and for your sake, not just mine, I really hope you do. 

That’s it for Summer Shorts, I hope you’ve enjoyed the series. The Everyday Style School will be back in a few weeks with a brand new look–and format!. Until then, thank you for listening and spending the summer with me. Remember your everyday matters, so get dressed for it! 

Jennifer Mackey-Mary [outro]: And that's a wrap. Thank you for listening today. If you're loving the Everyday Style School podcast, I'd like to invite you to become a member of the Style Circle. It's our monthly all-access membership that gives you everything we create to make style easy, so you can save time and money, have easier mornings, and more confidence all day long. You get our seasonal capsule wardrobe guides, all of the masterclasses we offer, and our exclusive members-only podcast, The Everyday Style School Extra Credit. Plus, you're invited to the Facebook community, where you can get even more style support and inspiration. I would love to get to know you and support your style journey. It's just $19 a month, less than the cost of a clearance shirt you're never gonna wear. Come join me and make your everyday style easier.